The transition into retirement isn’t just a financial shift- it’s a psychological one. We’re excited to have a special guest on the show this week. Josh Bell, coach and consultant at The Josh Bell Company, is joining us to explore what it really means to leave your job title behind and step into the unknown.
Jude and Josh will unpack the emotional and relational changes that can catch even the most prepared retirees off guard. From identity struggles to the need for new routines, they discuss what happens after the celebrations and bucket-list trips are over, and how a little pre-retirement reflection can go a long way.
Tune into this great conversation on building a retirement life filled with clarity, purpose, and healthy relationships!
📌 Here’s some of what we discuss in this episode:
🧭 Redefining your identity without your career title
🗓️ Designing new rhythms for your daily life
❤️ Navigating relationship shifts in retirement
🎯 The danger of retiring without a plan beyond finances
🎙️ How coaching can be helpful during big life transitions
0:00 – Intro
1:55 – Ambiguity and identity loss post-work
3:30 – “Who am I without this title?”
9:15 – Couples re-learning how to live together
12:11 – Daily, weekly, and monthly rhythms
14:47 – Finding purpose: what energizes you?
17:19 – The power of coaching + connecting with Josh
Learn more about Josh:
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Schedule your complimentary review with Jude: https://calendly.com/
Episode Transcript
Note: This transcript was produced using AI, so please excuse any typos and inaccuracies…
00:00
Flying high above the metropolis. It’s the Roth guy
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with holistic wealth advisor Jude Wilson.
Read More00:11
Time once again for another edition of the Roth guy with Jude Wilson, and this week, we’ve got a very special guest. Josh Bell is going to be joining us, and we’re going to be talking about the transition from working years to retirement, and the challenges that faces Josh is a coach and a consultant, so we’re looking forward to his insights this week on the program. So let’s get into it. Jude, take it away, my friend. Well, thank you, Mark. It’s a pleasure to have Josh on the show, because most of the time we’re talking financial strategy. We’re talking about how to get to retirement, how to reduce your taxable liability, how to basically live the lifestyle that you’ve been dreaming about. But we very rarely talk about the psychology of retirement. And when I’m meeting with clients, what I’ve noticed over my gosh, over 25 year career, people work so hard to get to that, that net worth and that place where they feel comfortable that they can finally make that transition, but what they rarely think about is, wow, I’ve got all this time on my hands and who was, who will I be in retirement, versus who I was in my working years. So the psychology of retirement is, to me, just as important as the finance of retirement, and that’s why I’m just so happy to have Josh on the show. Josh, how are you today? I’m doing so great. Jude, thank you so much for the invitation. I love the work that you’re doing. I love how you equip your clients, and I’m really looking forward to diving into this topic today. Well, so am I? I’m really excited because, as I said before, this is something we really talk about, and I have some stories to share with you of some very successful clients who built a great net worth but then had a difficult time transitioning. And so let’s start off by talking about, how do you approach helping people make that transition psychologically. What are some of the typical challenges that you see when people are trying to make a big transition in life? I think when, when folks that I work with, when clients that I work with are facing some sort of transition, whether it’s personal or professional, and they both really intersect with each other, right? There’s a lot of ambiguity, right? Because we don’t know the future. We try to be as prepared as possible for what’s ahead, but we don’t know every piece of that. And so when you’ve got a lot of ambiguity around what comes next, my job as someone’s coach is to come in and ask a lot of questions about what do you want and what are you looking for, and that way, we can take that ambiguity and get it a little bit more exact in terms of what you are trying to pursue in your next chapter, whatever that is, whether that’s retirement or just moving to a new career, I work with people across the spectrum in terms of what they are looking to do with their life. So when you can take that ambiguity and get a little bit more specific about what you want, then you know kind of where you’re headed, and we can chart a course to that. And I think that’s similar, probably to the financial planning that you do. You’ve got, like, a financial target, but you also need some targets around. Okay, you’ve figured out how to fund this chapter of your life. Now, what do you want to do with it? Exactly. I love the fact that you said the next chapter, because oftentimes we look at retirement as the finish line. I’ve worked hard. I’ve worked hard. I’m moving toward this goal, and I got here, but that’s when to quote you, where I see most of our clients, once they get to that line, have the ambiguity, who am I without this title? You know, whether I was a CEO, whether I was a doctor or a lawyer, who am I without this? So tell me a little bit about how do you find your identity when now you’re not Dr, so and so, or president, so and so. I think that we’re taught in our society that our work is who we are. It’s a very common thing when you meet someone for the first time, you don’t say who are you? That would kind of be a weird question we ask. What do you do, right? And so when it’s all based on what you do, and that’s the first thing that you think of when you think of who you are, when you change and step into a chapter where people don’t see you primarily as your profession. They see you in some other aspect, some other facet of your life. That’s really a
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moment where you look in the mirror and a lot of people ask, who am I? I’ve been devoting 40 plus hours of my life to this one particular thing for years, decades, the majority of my adult life.
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Right? So what do I stand for? Who am I in this space? Those questions? I think when you can start asking those questions before you get to that finish line of retirement, the transition is not as abrupt. When someone isn’t doing any pre work around that and they just get to retirement, they’re thinking about the celebration. They’re thinking about that trip they want to take right after retirement. They’re thinking about whatever just, oh, man, I’m not going to have to wake up at seven in the morning and be in the office by eight and get home at like 630 and whatever it is when they kind of get past that space of, okay, this is New World, new life, when they’ve done some pre work around that, when they’ve asked some questions about what they want prior to that, then they can get a little bit more prepared to face those the week after you get back from the trip or whatever it is, right? You know, I really enjoy that, because our job is to get them to the point where they can say, Okay, we have a definitive date. That’s when you know I’m gonna put in my letter of resignation. But what you’re saying is, in addition to that, there should be some pre work to figure out what’s gonna happen that very next week. And I mentioned to you that I have a couple of stories I want to share some of some of the client interactions that I’ve had, because a lot of our clients fit into, you know, one of these categories. The first category is my, my favorite type, type of client, because I identify with it. I’m a type, a type of person. I’m very goal oriented. And so we have clients who have been very successful in their first professional career, and once they retire, they don’t have, not only the title, but they don’t have the staff and the people that were helping them along the way. So one of my favorite stories is a client of mine, very successful VP at a major company and traveled probably 80% of the time for his job, he would he would be home maybe three days out of the week and traveling the rest once he retired, and his assistant booked all of his travel. He never touched the computer when it came to that once he retired, as you suspected, he and his wife took the big trip, they came back, and he was invited to speak at a conference. And he turned to his wife, after he got the invitation, and said, Honey, I was invited to speak at this conference. Do you think you can book my flight in my hotel? And she looked at him and said, I am not your assistant.
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And he was totally lost. And I think that moment gave him a shock about, holy cow, I am not that person anymore. How would you react to something like that? Well, I think that that is definitely a great example of you live in a certain world. You have a certain framework, you have certain sorts of support that are very much based in a professional context, right? And when you are transitioning into more of a space where it’s about your personal goals or your personal next steps, one of those things is definitely how you relate to the other people in your life, because your time has shifted, but also your expectations of them might shift. And that’s that’s a whole nother chapter. Like, how do you handle your relationships in retirement? Because the number of people I know who a spouse retires, and the other spouses, oh, my God, they’re here every day, you know. And I need you to get a hobby. I need you to start a sport. I need you to go on a trek. I don’t care, just get out of the house, right, right? So I think that those types of
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realities are definitely something that people have to navigate. I have a an uncle, actually, who retired recently, and his goal was to hike the Appalachian Trail, and that is what he is doing. And he is out of the house, he is doing his own thing, and that’s really working for him. And so I think that there’s the relational aspects, and then there’s also, you know, how do you want to pursue your time? How do you want to spend this next chapter? And you brought up something that I was talking was going to mention also, is the relational aspect between spouses. Another couple that I work with, one spouse had told me, you know, guys, I love not having to punch a clock anymore, or having to be at work at a specific time or work so many hours, but and he said to me, Jude, I love my wife, so don’t get me wrong when I say this, but she’s always there. Now
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and then, you know, I we were both at a cocktail party together, and I was talking to him one on one, and then he left to speak to someone else, and I was speaking to his wife, and I said to her, I said, How are you enjoying retirement? She says, I love it. But one problem, he.
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Is always around. And I thought they just said the same answer about themselves, so obviously they’re not communicating. So is the relational piece challenging? Also relearning your spouse, I guess at this point, well, you hear it all the time. When people go through some sort of major life transition, you hear it when someone becomes an empty nester. You hear it when something changes, or even when they when they have their first kid. It really changes the relational dynamic. It changes the time and energy that you can spend on yourself and another person. And when you’re used to having a lot of your time and energy taken up by your job, and a lot of your spouse’s time and energy taken up by their job or whatever else. It’s really a renegotiation moment of, okay, we’ve got this time on our hands. We’ve got discretionary time. We’ve got discretionary money, hopefully, if we plan for retirement,
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how much of this do we want to spend together and how much of this is an opportunity for us to figure out what we want to do so we can have something to talk about at the end of the day, because we didn’t do the exact same thing. Like, well, I was in the living room, you were in the kitchen. How’s the kitchen today? Like, that’s, that’s not exactly a stimulating, dimmer dinner conversation, right? So I think that that it’s really a space where both spouses can figure out, you know what, what do I want to spend my time and energy on? And the reality is that you’re probably going to have, hopefully, some differences there. And one of you might be a little clearer than the other on how you want to spend your time and energy, just because one spouse is has reached the retirement
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finish line. The other spouse may still be working, or they may have had a very active life outside of a professional life, and so letting each person figure out what works for them and what what you need to be able to do together and do separately, I think is a really key conversation, and the earlier you have it, the easier it will be. I love that. I think we’ve clearly defined that there is a need to address this prior to retirement. Because I think so many people think that, well, this is going to be a breeze. I’m going to spend more time with the with the grandkids. I’m going to play more golf. We’re going to go on more cruises, but you’re not going to do that 24 hours a day, seven days a week. So tell me, how would you approach or help our audience understand what are some things that they should be thinking about prior to retirement? What are some of the questions they should be asking or some of the interventions that they should be having with their spouse? How would you approach that? So I would say what I talk to all my clients about is, what are the rhythms of your life, and what do you want those rhythms to look like when you’re working your rhythm is you get up at a certain time you get to the office or in front of the computer by a certain time, work defines how you spend your day.
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As you’re approaching retirement, I would encourage you to think about what do you want your day to look like? Are you somebody who loves a good early morning? You want to wake up early, you want to go do something, physical exercise, be outside. You want to have breakfast together or separate.
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There can be some really mundane things that you think, Oh, we don’t need to talk about that. But generally speaking, when you say we don’t need to talk about that, you probably need to talk about it, right? If you just talk about because being on the same page in terms of expectations, someone might think, Oh, I get to have breakfast, lunch and dinner with my spouse every day, and I’m looking forward to that. And the spouse is like, no, no, I’m good. I need to have lunch with my friends. I need to be out of the house, you know? And if the more you can have that conversation and say, you know, what do we want a day to look like? What do we want this week to look like? Are there things that we want to schedule on a weekly basis that we do individually or separately? Are there things that we want to schedule on a monthly basis? How often are we thinking about going on a cruise? You might be one of those news stories where you sell everything and you live on a cruise ship. I’m guessing that’s the minority of your clients? Yeah, I’m just guessing, you know, but the more you can think about what are the daily rhythms you want, and what are the weekly rhythms, monthly rhythms, quarterly or annual rhythms, things that you want to go ahead and schedule. You probably haven’t done that with your personal life, as much most people don’t, but in retirement, it’s important to have that rhythm. You have to create it for yourself, instead of expecting work to do it for you. So what I’m hearing from you to kind of get to some questions or some a process, because I’m very process oriented, yeah, prior to retirement, you really and we.
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Talked about this earlier. I think one of the big questions is trying to identify, who will you be, without your title,
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and also then the next step, probably identifying, how do you design that life in retirement, like you said, What do I want my day to look like? And then from there, where would you take it? So I think being in a space of figuring out who you are is it sounds kind of like an odd question. The average person is probably more focused on what they do and their professional life and dealing with whatever is going on in their personal life, but when you can take a little bit of time to decide, you know, who am I? What makes me tick? What do I care deeply about?
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I’ve talked to folks who are going through a season where they’re trying to figure out what that looks like, and the questions that I encourage them to ask are, what makes you really excited and what makes you really frustrated, if something provokes a lot of really strong energy in you, it, it shows that you care about it, right? If it sometimes, I ask people, What, what do you really love doing? And sometimes folks, especially us type A folks, are so burnt out by work, they’re like, I don’t remember being excited lately, you know? So sometimes we have to nuance that a little bit. But if you can think of something you absolutely love that you could feel like you could spend a lot of time on, that might be something that you want to build into your life and build into your day. Maybe that’s volunteer work around a particular cause that you care a lot about. Maybe it’s a particular community that you’re part of, maybe it’s religious, maybe it’s more of an interest focused group,
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thinking about the things that you enjoy doing and that energize you, building that in. And you can start to build that in before you’re retired, you can start dipping your toe into something that you’ve always wanted to do. Okay, I’m gonna attend a meeting of that and see if it’s as interesting as it sounds to me, or maybe I go in the meeting like, nope, not spending my life on this right? So thinking about the things that you’re passionate about, whether it’s something that really excites you or something that really frustrates you, maybe that’s something where you want to spend some time now and then, maybe spend more time once you have more discretionary time. Yeah, I think that’s so perfect. And as I said in the beginning, I’ve got some stories to share with you. I’ll share one last story to highlight what you just talked about. I started noticing in my career, once some of my clients started to retire, that this might be an issue transitioning and having all of this time to yourself and one of my, one of my favorite clients, to two professionals. The husband was going to retire first, and I talked to him about this topic. And I’m great at finance, but I’m not trained to be a coach. But I thought, you know, this is a topic we should talk about. And I was mentioning to the husband, hey, you know you’re going to have all this free time. Have you ever thought about what you want to do? So, dude, I really didn’t think about it. I’m just glad to get to retirement. And I said there are so many people, young people, entering your profession that may need some mentorship. Have you ever thought about maybe teaching, volunteering and teaching a course or mentoring some young kids in college or high school. And he said, I have absolutely zero interest in that. I realized this is not my lane. And so I really think people like you provide a very valuable service. Tell tell us. How do you work with people? How can they get in contact with you if they want to talk about, you know, big transitions in their life, maybe not just retirement, but other transitions that they may be making sure. And I think that, I think you are really good at the work that you do, and just because you struck out once with somebody, you know, there might be other opportunities to make suggestions, but people can get in touch with me primarily through my website. It’s Josh w bell.com and there’s a contact form there. That’s probably the easiest way to do that. The way that I work with folks is they we come and have kind of an intro conversation that where I ask, you know what? What makes you think coaching is the right next step for you. And so that gives me the opportunity to hear, where are you, what are you looking to do? What is your primary kind of presenting issue and concern? And then I talk a little bit about how I work with folks. So it’s not my job to tell you what to do with your life. It’s my job to ask you good questions and help you get the clarity that you’re looking for, so that we can then build a plan that works for you to achieve the goals that you’re pursuing. And so that can really be any type of change in your life. But I love working with folks who are making big changes, because it’s exciting. It.
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To be anxiety producing, but it’s also an opportunity to make really positive changes in their life that you’re really going to enjoy and look forward to. So anytime somebody wants to come talk to me about that stuff, Sign me up. I’m happy to do it. That’s awesome. I don’t know about you, Mark, but I learned a lot today. How did you how did you feel about the conversation? I enjoyed the conversation. Great stuff indeed. And it is something that we don’t spend enough time about. You know, we talk often about the x’s and the O’s, but we don’t always dive into the y’s and the house. So great conversation this week again. Let me remind folks that if you need some help, reach out to Josh. We’re going to have the links in the show descriptions below, along with, of course, the always, present descriptions that we have for Jude, right? How to get in touch with Jude. So go to Josh w bell.com Again, or just check the links below. Josh is a executive coach and an organizational consultant, and certainly here to help you. So thanks so much for your time. We appreciate everybody being on the podcast today and checking out the podcast. Don’t forget to subscribe to us on Apple or Spotify or, course, YouTube hit that thumbs up and that subscribe button and that notification bell supports the channel as well as gets you new content when it comes out. Thank you so much for your time to Josh and to Jude as always here on the Roth guide, we’ll catch you next time.
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